Phenmetrazine
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Phenmetrazine
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| Systematic (IUPAC) name | |
| 3-methyl-2-phenylmorpholine | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| ChemSpider | |
| Chemical data | |
| Formula | C11H15NO |
| Mol. mass | 177.2456 |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | 8 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | Oral, Intravenous, Vaporized, Insufflated, Suppository |
Phenmetrazine is a sympathomimetic drug which acts as a stimulant in the central nervous system. It was previously sold as an anorectic under the trade name Preludin, but has since been removed from the market. It was initially replaced by the weaker analogue phendimetrazine (trade name Bontril), but this is now only rarely prescribed, due to problems with abuse.
Other trade names that have been used for Phenmetrazine include: Defenmetrazin, Fenmetrazin, Oxazimedrine, Phenmetraline.
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[edit] History
Phenmetrazine was first patented in Germany in 1952 by Boehringer-Ingelheim,[1] with some pharmacological data published in 1954.[2] It was the result of a search by Thomä and Wick for an anorectic drug without the side-effects of amphetamine.[3] Phenmetrazine was introduced into clinical use in 1954 in Europe.[4]
[edit] Medical use
In clinical use, phenmetrazine produces less nervousness, hyperexcitability, euphoria and insomnia than drugs of the amphetamine family.[5] It tends not to increase heart rate as much as other stimulants. Due to the relative lack of side effects, one study found it well tolerated in children.[3] In a study of the effectiveness on weight loss between phenmetrazine and dextroamphetamine, phenmetrazine was found to be slightly more effective.[6]
Even though the manufacturers claimed it had "exceptional safety and strikingly low incidence of side effects", within a few years there were reports of psychosis similar to that of amphetamine.[4]
[edit] Pharmacology
Phenmetrazine produces its action by causing release of noradrenaline and dopamine in the central nervous system.[7]
After an oral dose, about 70% of the drug is excreted from the body within 24 hours. About 19% of that is excreted as the unmetabolised drug and the rest as various metabolites.[8]
In trials performed on rats, it has been found that after subcutaneous administration of phenmetrazine, both optical isomers are equally effective in reducing food intake, but in oral administration the levo isomer is more effective. In terms of central stimulation however, the dextro isomer is about 4 times as effective in both methods of administration.[9]
[edit] Abuse
It has been abused in many countries, for example Sweden. When stimulant abuse first became prevalent in Sweden in the 1950s, phenmetrazine was preferred to amphetamine and methamphetamine by addicts. In the autobiographical novel "Rush" by Kim Wozencraft, intravenous phenmetrazine is described as the most euphoric and pro-sexual of the stimulants the author used.
Phenmetrazine was classified as a narcotic in Sweden in 1959, and was taken completely off the market in 1965. At first the illegal demand was satisfied by smuggling from Germany, and later Spain and Italy. At first, Preludin tablets were smuggled, but soon the smugglers started bringing in raw phenmetrazine powder. Eventually amphetamine became the dominant stimulant of abuse because of its greater availability.
Phenmetrazine was taken by The Beatles early in their career. Paul McCartney was one known user. McCartney's introduction to drugs started in Hamburg, Germany. The Beatles had to play for hours, and they were often given "Prellies" (Preludin) by the maid that cleaned their housing arrangements, German customers, or by Astrid Kirchherr (whose mother bought them). McCartney would usually take one, but John Lennon would often take four or five.[10][verification needed] Hunter Davies asserted, in his 1968 biography of the band,[11] that their use of such stimulants then was in response to their need to stay awake and keep working, rather than a simple desire for kicks.
[edit] References
- ^ ALBERT BOEHRINGER; ERNST BOEHRINGER. Improvements in or relating to the preparation of substituted morpholines. GB773780.
- ^ Thomä, O and Wick, H (1954). "Über einige Tetrahydro-1,4-oxazine mit sympathicomimetischen Eigenschaften". Arch. Exp. Path. Pharm 222: 540.
- ^ a b Martel, Antonio (1957). "Preludin (Phenmetrazine) in the Treatment of Obesity". Can. Med. Assoc. J. 76: 117.
- ^ a b Kalant, Oriana Josseau (1966). The Amphetamines: Toxicity and Addiction.
- ^ "Phenmetrazine Hydrochloride". J. Am. Med. Assoc. 163 (5): 357. 1957.
- ^ Hampson, J (1960). "Phenmetrazine and Dexamphetamine in the Management of Obesity". The Lancet 275 (7137): 1265. doi:.
- ^ Rothman RB et al. (2002). "Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain.". European Journal of Pharmacology 447 (1): 51. doi:. http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=12106802.
- ^ Anthony C Moffat, M David Osselton and Brian Widdop. Clarke's Analysis of Drugs and Poisons. ISBN 0-85369-473-7.
- ^ Engelhardt, A (1961). "Studies of the Mechanism of the Anti-Appetite Action of Phenmetrazine". Biochem. Pharmacol. 8 (1): 100. doi:.
- ^ Miles 1998. pp66-67.
- ^ Hunter Davies: The Authorized Biography. McGraw-Hill. 1968 p78
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